Hydrochloric Acid → (7-Nitroindol-1-yl)-acetic acid

HRID 571196Notes

Reaction equation

HRID 571196 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[N:11]([CH2:13][C:14]([O:16]C)=[O:15])[CH:10]=[CH:9]2)([O-:3])=[O:2].[Li+].[OH-].Cl>C1COCC1>[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[N:11]([CH2:13][C:14]([OH:16])=[O:15])[CH:10]=[CH:9]2)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 86681614methyl 2-(7-nitro-1H-indol-1-yl)acetate

Product 1

HCID 68424240(7-Nitroindol-1-yl)-acetic acidYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-(7-nitro-1H-indol-1-yl)acetate (0.37 g, 1.580 mmol) in THF (20 ml), LiOH 1N (3.16 ml, 3.16 mmol) was added at room temperature. The reaction was stirred at the same temperature for 16 hours. Aqueous 2N HCl was added and the solvent was partially removed under vacuum. The remaining aqueous phase was extracted with ethyl acetate; the organic phase was dried over sodium sulfate and the solvent was evaporated under vacuum affording 2-(7-nitro-1H-indol-1-yl)acetic acid (0.33 g, 1.499 mmol, 95% yield). MS/ESI+ 220.9 [MH]+. This compound was used without any additional purification.

Workup

  1. customthe solvent was partially removed under vacuum
  2. extractionThe remaining aqueous phase was extracted with ethyl acetate
  3. dry with materialthe organic phase was dried over sodium sulfate
  4. customthe solvent was evaporated under vacuum

Sources & evidence

ORD record
ord-ac45c9b0380145d2bf04389534a6b83b
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

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